Thermally stable alignment materials

Abstract

A thermally stable diamine compound of formula (I′) is proposed as well as polymers, copolymers, polyamic acids, polyamic acid esters, or polyimides based on such compound. Also, a process of preparing orientation layers for liquid crystals including preparing orientation layers for liquid crystals from thermally stable alignment materials comprising diamine compounds of formula (I′).

What is claimed is: 
     
         1 . A process of preparing orientation layers for liquid crystals, comprising preparing orientation layers for liquid crystals from thermally stable alignment materials comprising diamine compounds of formula (I′), 
       
         
           
           
               
               
           
         
         wherein, 
         A represents an unsubstituted or substituted carbocyclic or heterocyclic aromatic group selected from a monocyclic ring of five or six atoms, two adjacent monocyclic rings of five or six atoms, a bicyclic ring system of eight, nine or ten atoms, or a tricyclic ring system of thirteen or fourteen atoms; and 
         wherein 
         B represents a straight-chain or branched C 1 -C 16 alkyl group, which is unsubstituted or substituted by
 di-(C 1 -C 16 alkyl)amino, C 1 -C 6 alkyloxy, nitro, cyano, and/or halogen selected from fluorine, chlorine, bromine or iodine; and wherein one or more —CH 2 — group may independently from each other be replaced by a linking group; 
 
         D is a selected from the group of the following compounds: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         “ ” denotes the linking(s) of D to S 1  in compound (I) and represents a single bond; and 
         S 0  represents a single bond or a spacer unit, which is a straight-chain or branched, substituted or unsubstituted C 1 -C 24 alkylene, wherein one or more —CH 2 — group may be replaced by a linking group; 
         M represents a H, C 1 -C 24 alkyl and CF 3 , 
         L is —CH 3 , —COCH 3 , —OCH 3 , nitro, cyano, halogen, CH 2 ═CH—, CH 2 ═C(CH 3 )—, CH 2 ═CH—(CO)O—, CH 2 ═CH—O—, —NR 5 R 6 , CH 2 ═C(CH 3 )—(CO)O— or CH 2 ═C(CH 3 )—O—, 
         wherein: 
         R 5 , R 6  each independently from each other represents a hydrogen atom or C 1 -C 6 alkyl; 
         u 3  is an integer from 0 to 2·
 and/or an alicyclic group; 
 
         E represents an aromatic group, an oxygen atom, a sulphur atom, —NH—, —N(C 1 -C 6 alkyl)-, —CR 2 R 3 ,
 wherein R 2  and R 3  are independently from each other hydrogen or a cyclic, straight-chain or branched, substituted or unsubstituted C 1 -C 24 alkyl, wherein one or more —CH 2 — group(s) may be independently from each other replaced by a linking group, and with the proviso that at least one of R 2  and R 3  is not hydrogen; 
 
         S 1  represents a single bond or a cyclic, straight-chain or branched, substituted or unsubstituted C 1 -C 24 alkylene, if D is a compound of formulae IIa, IIc, IId, IIe, IIf, IIg, IIh, IIi, IIj, IIk; and if D is a compound of formula IIb, S 1  represents a single bond or a cyclic, straight-chain or branched, substituted or unsubstituted C 2 -C 24 alkylene; 
         S 2  represents a spacer unit; 
         X, Y each independently from each other represents hydrogen, fluorine, chlorine, cyano, unsubstituted or with fluorine substituted C 1 -C 12 alkyl, in which one or more —CH 2 — groups may be replaced by a linking group; 
         n, n1 each independently from each other represents 1, 2, 3 or 4; 
         with the proviso that if n is 2, 3, or 4, each A, B, x 1 , E, S 1 , S 2 , X, Y are identical or different; and if n1 is 2, 3 or 4 each B, x 1  is identical or different. 
       
     
     
         2 . The process according to  claim 1 , wherein the diamine is a compound of formulae (VI), (VII), (VIII), (IX), (X), (XI), (XIa) and (XIb) 
       
         
           
           
               
               
           
         
         wherein in (VII) and (VIII) S 1  represents a single bond or a cyclic, straight-chain or branched, substituted or unsubstituted C 2 -C 24 alkylene; the other substituents have the same meaning as given below for (VI), (IX), (X), (XI), (XIa), (XIb), (XIc) and (XId) 
       
       
         
           
           
               
               
           
         
         wherein 
         A, B, x 1 , n, n1, D, E, M, S 2 , S 1 , S 0 , X and Y have the above given meanings as in  claim 1  and R 5 , R 6  have the same meanings as in  claim 1 ; 
         L is —CH 3 , —OCH 3 , —COCH 3 , nitro, cyano, halogen, CH 2 —CH—, CH 2 ═C(CH 3 )—, CH 2 ═CH—(CO)O—, CH 2 ═CH—O—, CH 2 ═C(CH 3 )—(CO)O—, or CH 2 ═C(CH 3 )—O—, 
         u 3  is an integer from 0 to 2. 
       
     
     
         3 . The process according to  claim 1 , wherein the orientation layer comprises coated and uncoated areas, whereby the surface of the uncoated areas is not contaminated during the thermal baking in the process of preparation of an orientation layer. 
     
     
         4 . The process according to  claim 1 , wherein the uncoated areas have a surface energy of >40 mN/Meter on ITO coated glass plates. 
     
     
         5 . The process according to  claim 1 , wherein S 0  represents a single bond or a spacer unit, which is a straight-chain or branched, substituted or unsubstituted C 1 -C 6 alkylene, wherein one or more —CH 2 — group may be replaced by a linking group. 
     
     
         6 . The process according to  claim 1 , wherein the one or more —CH 2 — group are non-adjacent —CH 2 — groups. 
     
     
         7 . The process according to  claim 5 , wherein the one or more —CH 2 — group are non-adjacent —CH 2 — groups. 
     
     
         8 . The process according to  claim 1 , wherein S 0  represents a single bond or a spacer unit, which is a straight-chain or branched, substituted or unsubstituted C 24 alkylene, wherein one or more —CH 2 — group may be replaced by —O—, —O(CO)—, —(CO)O—, —NR 1 CO—, —CONR 1 —, wherein R 1  is hydrogen or C 1 -C 6 alkyl. 
     
     
         9 . The process according to  claim 1 , wherein S 0  represents a single bond or a spacer unit, which is a straight-chain or branched, substituted or unsubstituted C 1 -C 6 alkylene, wherein one or more —CH 2 — group may be replaced by —O—, —O(CO)—, —(CO)O—, —NR 1 CO—, —CONR 1 —, wherein R 1  is hydrogen or C 1 -C 6 alkyl. 
     
     
         10 . The process according to  claim 8 , wherein the one or more —CH 2 — group are non-adjacent —CH 2 — groups. 
     
     
         11 . The process according to  claim 9 , wherein the one or more —CH 2 — group are non-adjacent —CH 2 — groups. 
     
     
         12 . The process according to  claim 1 , wherein S 0  represents a single bond. 
     
     
         13 . The process according to  claim 2 , wherein in (VII) and (VIII) S 1  represents a single bond or a cyclic, straight-chain or branched, substituted or unsubstituted C 5 -C 24 alkylene. 
     
     
         14 . The process according to  claim 2 , wherein in (VII) and (VIII) S 1  represents a single bond or a cyclic, straight-chain or branched, substituted or unsubstituted C 10 -C 24 alkylene.